Photochromic properties of thienylpyrrole azo dyes in solution

被引:69
作者
Coelho, PJ [1 ]
Carvalho, LM
Fonseca, AMC
Raposo, MMM
机构
[1] Univ Trasos Montes & Alto Douro, Ctr Quim Vila Real, P-5001801 Vila Real, Portugal
[2] Univ Minho, Ctr Quim, P-4710057 Braga, Portugal
关键词
photochromism; heterocyclic azo dyes; thienylpyrroles; aggregation;
D O I
10.1016/j.tetlet.2006.03.125
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The photochromic behaviour of thienylpyrrole azo dyes in THF Solutions was Studied for the first time. The photochromic properties are strongly dependent on the substitution pattern on the dyes. Nitro-substituted thienylpyrrole azo dyes are particularly interesting since they exhibit very fast colouration/decolouration processes. The activation energies of these compounds are among the lowest values reported for heterocyclic azo dyes. These compounds show aggregation phenomena in freshly prepared solutions of THF. which lead to variable photochromic behaviours. Only after 1-5 h the solutions reach equilibrium and then reproducible photochromic behaviour can be observed. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3711 / 3714
页数:4
相关论文
共 22 条
[1]   FURTHER KINETIC EVIDENCE FOR THE COMPETITIVE ROTATIONAL AND INVERSIONAL Z-E ISOMERIZATION OF SUBSTITUTED AZOBENZENES [J].
ASANO, T ;
OKADA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (23) :4454-4458
[2]   THERMAL Z-E ISOMERIZATION OF AZOBENZENES - THE PRESSURE, SOLVENT, AND SUBSTITUENT EFFECTS [J].
ASANO, T ;
OKADA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (23) :4387-4391
[3]   Five-membered rings as diazo components in optical data storage devices:: an ab initio investigation of the lowest singlet excitation energies [J].
Åstrand, PO ;
Sommer-Larsen, P ;
Hvilsted, S ;
Ramanujam, PS ;
Bak, KL ;
Sauer, SPA .
CHEMICAL PHYSICS LETTERS, 2000, 325 (1-3) :115-119
[4]  
Barachevsky VA, 2002, ZH NAUCH PRIKL FOTOG, V47, P4
[5]   CIS-TRANS ISOMERISM IN PYRIDYL ANALOGS OF AZOBENZENE - KINETIC AND MOLECULAR-ORBITAL ANALYSIS [J].
BROWN, EV ;
GRANNEMAN, GR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (03) :621-627
[6]   Aggregation of azo dyes with cationic amphiphiles at low concentrations in aqueous solution [J].
Buwalda, RT ;
Jonker, JM ;
Engberts, JBFN .
LANGMUIR, 1999, 15 (04) :1083-1089
[7]   Spectrokinetic studies on new bi-photochromic molecules containing two naphthopyran entities [J].
Coelho, PJ ;
Salvador, MA ;
Heron, BM ;
Carvalho, LM .
TETRAHEDRON, 2005, 61 (49) :11730-11743
[8]   Linear and nonlinear optical properties of photochromic molecules and materials [J].
Delaire, JA ;
Nakatani, K .
CHEMICAL REVIEWS, 2000, 100 (05) :1817-1845
[9]   Using light to control physical properties of polymers and surfaces with azobenzene chromophores [J].
El Halabieh, RH ;
Mermut, O ;
Barrett, CJ .
PURE AND APPLIED CHEMISTRY, 2004, 76 (7-8) :1445-1465
[10]   Three-dimensional optical data storage using photochromic materials [J].
Kawata, S ;
Kawata, Y .
CHEMICAL REVIEWS, 2000, 100 (05) :1777-1788